A novel stereoselective [8+2] double cycloaddition route to hydronaphthalene ring systems

Abstract Substituted hydronaphthalenes where each of the ten carbons of the two-ring system contains a functionality were obtained through a tandem [8+2] cycloaddition and base-catalyzed rearrangement process using dienylfurans and electron-deficient alkynes. If the [8+2] process is conducted under solvent-free conditions the process could be conducted in a single reaction flask without isolation of the chromatographically sensitive [8+2] cycloadducts. A mechanism involving base catalyzed alkene positional isomerization followed by disrotatory electrocyclic ring closure was proposed for the key reaction step that converts [8+2] cycloadducts to hydronaphthalenes. The products undergo selective ring opening–isomerization processes upon treatment with Lewis acids.